Fuhrhop J., Penzlin G. — Organic Synthesis: Concepts, Methods, Starting materials :: Электронная библиотека попечительского совета мехмата МГУ

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Fuhrhop J., Penzlin G. — Organic Synthesis: Concepts, Methods, Starting materials

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Название: Organic Synthesis: Concepts, Methods, Starting materials

Авторы: Fuhrhop J., Penzlin G.

Язык:

Рубрика: Химия/

Статус предметного указателя: Готов указатель с номерами страниц

ed2k: ed2k stats

Издание: second edition, rewise and enlarged

Год издания: 1994

Количество страниц: 432

Добавлена в каталог: 29.10.2005

Операции: Положить на полку | Скопировать ссылку для форума | Скопировать ID

Предметный указатель

Acetate, piperidinium, cat. for aldol add.      82
Acetate, sodium, $\alpha$ -epimerization of ketones      277
Acetate, sodium, opening of oxiranes      282
Acetic acid, (dialkoxyphosphinyl)-, esters, pr.      188
Acetic acid, (dialkoxyphosphinyl)-, esters, Wittig — Horner olefinations      267 282
Acetic acid, anhydride ( $\mathrm{Ac_{2}O}$ ), protection with      see “Protection”
Acetic acid, anhydride ( $\mathrm{Ac_{2}O}$ ), Pummerer rearr. with      51 265
Acetic acid, bromo-, esters, $a^{2}$ -synthon      19 65 309
Acetic acid, bromo-, esters, $d^{2}$ -synthon      19 301
Acetic acid, bromo-, esters, pr.      179
Acetic acid, chloro-, esters, hydantoins from      308
Acetic acid, chloro-, esters, pr.      179
Acetic acid, cyano-, esters, pr.      177
Acetic acid, cyano-, esters, pyrrolines from      298
Acetic acid, diazo-, ethyl ester, cyclopropanes from      74—75
Acetic acid, diazo-, ethyl ester, pr.      176 178
Acetic acid, dichloro-, deblocking of pixyl ethers      342
Acetic acid, esters      see “Protection of hydroxy groups”
Acetic acid, esters, 1-methylethenyl ester, pr.      174
Acetic acid, esters, 1-methylethenyl ester, transenolization      58
Acetic acid, esters, C-H acidity      10
Acetic acid, hydroxy-, esters, pr.      176
Acetic acid, hydroxyphenyl-, (S)- (L-mandelic acid), chiral auxiliary (Masamune ketone) from      62
Acetic acid, mercapto-, redn. of methionine S-oxide      229
Acetic acid, oxo-, esters, 1-nitroalkanes      301
Acetic acid, oxo-, esters, pr.      176
Acyloin coupling      53—54
Acyloin coupling, retro-synthetic transform      194
Acyloins      see “Ketones
Adams’ hydrogenation catalyst (Pt on $\mathrm{PtO_{2}}$ )      105
Adoc protective group      229
Affinity cleavage of DNA      342
AIBN      see “Propanenitrile 2
Alcohols, 2-halo-      see “Halohydrins”
Alcohols, allylic, asym. epoxidation      124—127 265 321—325
Alcohols, allylic, pr.      174
Alcohols, allylic, selective oxidation      133—135
Alcohols, allylic, substitution by amines [Pd]      164 303
Alcohols, allylic, synthesis, 1-alkenylation of carbonyl compds      44—45 62—63 323 326—327
Alcohols, allylic, synthesis, alkylation of 2-enals      303 321 322
Alcohols, allylic, synthesis, allylic oxidation of alkenes      116 119—123
Alcohols, allylic, synthesis, opening of oxiranes with strong bases      27
Alcohols, allylic, synthesis, reduction of 2-enones      105—107
Alcohols, conversions to alkenes      see “ $\beta$ -Eliminations”
Alcohols, conversions to amines      160—161 267
Alcohols, conversions to halides      32 160—161 169 203 266 269 272 281 282
Alcohols, conversions to thiols      169
Alcohols, homoallylic, stereoselective      66—69 325—326
Alcohols, inversion-esteriflcation      160—161 286
Alcohols, Mitsunobu-type substitutions      160—161
Alcohols, oxidation to aldehydes      133—135
Alcohols, oxidation to carboxylic acids      134—135 319—320
Alcohols, oxidation to carboxylic esters      134—135
Alcohols, oxidation to ketones      109 111 133 135 266—267 276—277 283 322—323 328—329 337
Alcohols, oxidative cleavage of tert. alcohols      136
Alcohols, protection      see “Protection of hydroxy groups”
Alcohols, protection, reduction to alkanes      97 113—114 203
Alcohols, synthesis from alkenes      107—108 117 130—131 283 319—320 325 337
Alcohols, synthesis from carbonyl compounds by alkylation      44—45 321—323
Alcohols, synthesis from carbonyl compounds by ox. cleavage      136—137 282 283
Alcohols, synthesis from carbonyl compounds by redn.      96 98—99 103—108 274—275 283 319—320 325 326 349
Alcohols, synthesis from carbonyl compounds by redn., enantioselective      102—103 108
Alcohols, synthesis from oxiranes by alkylation      21 44 269
Alcohols, synthesis from oxiranes by reduction      98—99 113—114 274—275 319—320
Alcohols, synthesis from prim, amines      202—203
Aldehydes with 2-enoic esters ( $\mathrm{SmI_{2}}$ )      69
Aldehydes, $\alpha$ -alkylated      13
Aldehydes, $\alpha$ -alkylated, opt. active      25—26
Aldehydes, $\alpha$ -amino-, enol ether + CINO      268
Aldehydes, $\alpha$ -chloro-, ketone + $\mathrm{LiCHCl_{2}}$       51—52
Aldehydes, $\alpha$ -hydroxy-      49 50 51 121—122 267
Aldehydes, $\alpha,\beta$ -unsaturated, ketone + $\mathrm{LiCHCl_{2}}$       51—52
Aldehydes, $\beta,\gamma$ -unsaturated      70 76
Aldehydes, $\gamma$ -hydroxy-      63—64
Aldehydes, 1-alkenylations      323
Aldehydes, 1-alkynylations      303
Aldehydes, 1-allylations      44—45 66—69 323—326
Aldehydes, aldol type reactions      44—45 56—58 60—62 322—323
Aldehydes, conversion to $\alpha$ -hydroxynitriles etc.      18 50
Aldehydes, conversion to ketones      22 166
Aldehydes, conversion to Mannich iminium reagents      57 291—292
Aldehydes, conversion to sec. alcohols with RZnBr      44—45 301
Aldehydes, olefination      28—34 41 272—273 276 334
Aldehydes, oxidation to RCOOH or RCOOR'      134—135
Aldehydes, oxo-      see “Dioxo compounds”
Aldehydes, reduction to alcohols      98 105—106 302
Aldehydes, reduction to alkanes      98
Aldehydes, reduction to amines (via aldoximes or aldimines)      98
Aldehydes, reductive coupling      53
Aldehydes, synthesis, formylation of RX      46—47
Aldehydes, synthesis, hydration of 1-alkynes      117 131
Aldehydes, synthesis, hydroformylation of 1-alkenes      47—48
Aldehydes, synthesis, hydrolysis of 1,3-dithianes      79 328—329
Aldehydes, synthesis, hydrolysis of aci-nitroalkanes      16 65—66
Aldehydes, synthesis, oxidation of alcohols      117 133—135 325
Aldehydes, synthesis, oxidative cleavage of 1,2-diols      81—82 202 272—273
Aldehydes, synthesis, oxidative cleavage of alkenes      81—82 87—88 202 259 322 323 326
Aldehydes, synthesis, oxidative cleavage of oxiranes      88
Aldehydes, synthesis, oxidative rearr. of alkenes      129—130
Aldehydes, synthesis, Pummerer rearr. of sulfoxides      51
Aldehydes, synthesis, reduction of carboxamides      96 98 105
Aldehydes, synthesis, reduction of carboximidic esters      13 22—23 63—64 298
Aldehydes, synthesis, reduction of carboxylic anhydrides or halides      46—47 98
Aldehydes, synthesis, reduction of carboxylic esters      105—106 159 165 203 272—273 276 283 321 322 327—328 334
Aldehydes, synthesis, reduction of nitriles      50 111—112 298
Aldehydes, synthesis, reductive formylation of ketones      48—49
Aldehydes, umpolung      17 51
Aldol-type reactions      55—62 81—83 328—329
Aldol-type reactions, acid-catalyzed      55—59 81 93 208 279
Aldol-type reactions, diastereoselective      60—62 322—323
Aldol-type reactions, directed      55—62
Aldol-type reactions, enantioselective      59 61—62
Aldol-type reactions, retro-      see “Retro-aldol type cleavage”
Alkali metals, redn. with      see “Birch reduction”
Alkaloids      289—299
Alkaloids, pr.      290
Alkaloids, syntheses, electrocyclic reactions      153—154 295—299
Alkaloids, syntheses, Mannich/Vilsmeier type reactions      291—293
Alkaloids, syntheses, phenol and aryl coupling      293—295
Alkanes, branched, carbosulfenylation of alkenes      21
Alkanes, branched, hydromethylation of alkenes      105
Alkanes, halo-      see “Haloalkanes”
Alkanes, oxidation      118—119 285—286
Alkanes, synthesis by reduction by reductive cleavage of nitriles      280
Alkanes, synthesis by reduction by reductive coupling, of alkenes      37
Alkanes, synthesis by reduction by reductive coupling, of halides      36
Alkanes, synthesis by reduction of alcohols      97 113—114 203
Alkanes, synthesis by reduction of alkenes      96—97 101—105
Alkanes, synthesis by reduction of arenes      103—104
Alkanes, synthesis by reduction of carbonyl groups      98 109
Alkanes, synthesis by reduction of cyclopropanes      76 105
Alkanes, synthesis by reduction of halides      83 114—115 275 287 319—320 335—336
Alkenes (carbon-carbon double bonds), acidity of allylic C-H      9—10
Alkenes (carbon-carbon double bonds), alkoxy-      see “Enol ethers”
Alkenes (carbon-carbon double bonds), carbosulfenylation (addn. of “ $\mathrm{ArS^{+}R^{-}}$ ”)      21
Alkenes (carbon-carbon double bonds), conversion to aldehydes, ketones and tert. alcohols with borane + CO      9 47—48
Alkenes (carbon-carbon double bonds), coupling with organyl halides      42—43
Alkenes (carbon-carbon double bonds), double-bond shift      85 90—91 101 274 278
Alkenes (carbon-carbon double bonds), E/Z isomerizn      31 100—102 282 296 332
Alkenes (carbon-carbon double bonds), E/Z isomerizn via trans-glycol thiocarbonates      142
Alkenes (carbon-carbon double bonds), halo- (vinyl halides), from alkynes      132 325
Alkenes (carbon-carbon double bonds), hydration via boranes      107—108 130—131 319—320 325 337
Alkenes (carbon-carbon double bonds), hydration with mercury (2+)      283
Alkenes (carbon-carbon double bonds), hydromethylation      105
Alkenes (carbon-carbon double bonds), oxidation      117 123—130
Alkenes (carbon-carbon double bonds), oxidation to 1,2-dihalides      84 119 123—124 156—157
Alkenes (carbon-carbon double bonds), oxidation to 1,2-diols      123—124 127—130 276—277
Alkenes (carbon-carbon double bonds), oxidation to 1,3-dienes      123—124 333—334
Alkenes (carbon-carbon double bonds), oxidation to halohydrins      77 117 275—276 286—287
Alkenes (carbon-carbon double bonds), oxidation to halolactones      275 319—321 335—336

Alkenes (carbon-carbon double bonds), oxidation to oxiranes by epoxidation      18 123—127 156—157 265 321—325
Alkenes (carbon-carbon double bonds), oxidation to oxiranes via halohydrins      77 117 287 319—320
Alkenes (carbon-carbon double bonds), oxidative cleavage      81—82 87—89 259 280 282 322 323 326
Alkenes (carbon-carbon double bonds), oxidative rearrangement      129—130
Alkenes (carbon-carbon double bonds), protection      see “Protection of carbon-carbon double bonds”
Alkenes (carbon-carbon double bonds), reduction with $\mathrm{H_{2}}$ /cat      96—97 101—103 278 283
Alkenes (carbon-carbon double bonds), reduction with (Z)-diazene      102
Alkenes (carbon-carbon double bonds), reduction with alkali metals      103—104 278
Alkenes (carbon-carbon double bonds), reduction with boranes      89—90 97 130—131
Alkenes (carbon-carbon double bonds), sterically hindered, snythesis      33—35 41
Alkenes (carbon-carbon double bonds), sulfonation with $\mathrm{SO_{3}}$       252
Alkenes (carbon-carbon double bonds), synthesis      28—44 (see also “ $\beta$ -Eliminations”)
Alkenes (carbon-carbon double bonds), synthesis, cis-stereoselective      28—31 37 64 100—101
Alkenes (carbon-carbon double bonds), synthesis, olefination of carbonyl groups      28—35 110 125 267 272—273 276 281—283 334
Alkenes (carbon-carbon double bonds), synthesis, ox. dimerization of P ylides      31
Alkenes (carbon-carbon double bonds), synthesis, reduction of alkynes      40 64 100—101
Alkenes (carbon-carbon double bonds), synthesis, reductive coupling of alkynes      37—38
Alkenes (carbon-carbon double bonds), synthesis, reductive dimerization of carbonyl groups      34—35 41
Alkenes (carbon-carbon double bonds), synthesis, Tebbe methylenation of esters      110
Alkenes (carbon-carbon double bonds), synthesis, umpolung      18 211
Alkyl anions      4—5
Alkyl halides      see “Haloalkanes”
Alkyl synthons      see “Acceptor synthons” “Donor
Alkynes      see “1-Alkynes”
Alkynes, acid-catalysed cyclization      91—92 279—280
Alkynes, alcohol addition to      64
Alkynes, hydration via boranes      117 131
Alkynes, hydration, with mercury(2+)      52 57 117
Alkynes, hydroboration and coupling      37—38
Alkynes, hydrobromination/hydrozirconation      132 325
Alkynes, oxidation or ox. cleavage      117 132
Alkynes, reduction to alkenes with $\mathrm{H_{2}}$ [catalyst]      40 64 96—97 100—101 155
Alkynes, reduction to alkenes with DIBAL      100
Alkynes, reduction to alkenes with Li or Na      96—97 100—101
Alkynes, synthesis, alkynylation of RX      36 64 325
Alkynes, synthesis, fragmentation of hydrazones      89 142
Alkynes, synthesis, methylidynation with $\mathrm{N_{2}CHPO(OR)_{2}}$       325
Allyl a-synthons      22 27 299 303 325—326
Allyl d-synthons      66—69 90
Aluminate(1-), hydrotris(2-methyl-2-propanolato)-, redn. with      47—48 107
Aluminate(1-), tetrahydro-, lithium, + $\mathrm{AlCl_{3}} (3:4) [\rightarrow\mathrm{AlH_{3}}]$ , redn. with, reduction with, of $\alpha,\beta$ -unsaturated ketones      105—106
Aluminate(1-), tetrahydro-, lithium, + $\mathrm{AlCl_{3}} (3:4) [\rightarrow\mathrm{AlH_{3}}]$ , redn. with, reduction with, of pyridines      112—113
Aluminate(1-), tetrahydro-, lithium, chiral reducing agents from      107—108
Aluminate(1-), tetrahydro-, lithium, reduction with, of alkyl tosylates      114
Aluminate(1-), tetrahydro-, lithium, reduction with, of carboxamides      112—113 247 291
Aluminate(1-), tetrahydro-, lithium, reduction with, of carboxylic esters      325 326 328 349
Aluminate(1-), tetrahydro-, lithium, reduction with, of ketones      106—107 322—323
Aluminate(1-), tetrahydro-, lithium, reduction with, of nitriles      50 298
Aluminate(1-), tetrahydro-, lithium, reduction with, of oxiranes      114
Aluminate(1-), tris(alkanolato)hydro-, prepn.      96
Aluminate(1-), tris(alkanolato)hydro-, redn. with      98 107—108
Aluminum amalgam (Al-Hg), $\alpha$ -deoxygenation of $\alpha$ -hydroxy ketones      277
Aluminum chloride ( $\mathrm{AlCl_{3}}$ ), Lewis acid catalyst for aldol type reactions      81
Aluminum chloride ( $\mathrm{AlCl_{3}}$ ), Lewis acid catalyst for alkyne cyclotrimerization      330
Aluminum chloride ( $\mathrm{AlCl_{3}}$ ), Lewis acid catalyst for Friedel — Crafts reactions      15—16 291
Aluminum chloride ( $\mathrm{AlCl_{3}}$ ), Lewis acid catalyst for glycosyl chloride synthesis      266
Aluminum chloride ( $\mathrm{AlCl_{3}}$ ), Lewis acid catalyst for redn. with $\mathrm{LiAlH_{4}}$       105—106 112—113
Aluminum hydride ( $\mathrm{AlH_{3}}$ )      105—106 112—113
Aluminum oxide ( $\mathrm{Al_{2}O_{3}}$ ), basic cat.      32
Aluminum tris(2-propanolate), Oppenauer oxn. with      117 133—134 278
Aluminum(1+), diethyl-, sulfate ( $\mathrm{[Et_{2}Al]_{2}SO_{4}}$ ), catalyst for carbonyl allyl-stannylation      66—67
Aluminum, chlorodiethyl- ( $\mathrm{Et_{2}AlCl}$ ), catalyst for alkynylation of oxiranes      64—65
Aluminum, chlorodiethyl- ( $\mathrm{Et_{2}AlCl}$ ), catalyst for “ene” reaction of 2-alkynoic esters      282
Aluminum, hydrobis(2-methylpropyl)- ( $\mathrm{Bu_{2}^{i}AlH}$ , DIBAL), reduction with, 4-methoxybenzylidene acetals      326
Aluminum, hydrobis(2-methylpropyl)- ( $\mathrm{Bu_{2}^{i}AlH}$ , DIBAL), reduction with, alkynes      97 100
Aluminum, hydrobis(2-methylpropyl)- ( $\mathrm{Bu_{2}^{i}AlH}$ , DIBAL), reduction with, carboxamides      98
Aluminum, hydrobis(2-methylpropyl)- ( $\mathrm{Bu_{2}^{i}AlH}$ , DIBAL), reduction with, carboxylic esters      105—106 282 283 334
Aluminum, hydrobis(2-methylpropyl)- ( $\mathrm{Bu_{2}^{i}AlH}$ , DIBAL), reduction with, lactones      105 159 165 203 273 276 321 322
Aluminum, hydrobis(2-methylpropyl)- ( $\mathrm{Bu_{2}^{i}AlH}$ , DIBAL), reduction with, nitriles      50 96 111—112
Amfepramone, ( $\pm$ )-      302
Amidation      see “Carboxamides”
Amide, bis(trimethylsilyl)-      see “Silanamine ...”
Amide, diisopropyl-      see “2-Propanamine ...”
Amides, alkali, basicity      5 10
Amides, alkali, deprotonation with, of acidic C-H      10 300 303—304
Amides, alkali, of 1-alkynes      5 36 64
Amides, alkali, of haloalkanes      74—75 92
Amines, allylic or benzylic, reductive cleavage      97—98 113—114
Amines, allylic or benzylic, synthesis      164 303
Amines, protection      see “Protection”
Amines, synthesis by reduction of carboxamides      98 111—112 247
Amines, synthesis by reduction of imines      112—113
Amines, synthesis by substitution of allylic acetates      164
Amino sugars      263 267—268
Ammonia, deblocking with, of O-acyl derivatives      157—158
Ammonia, deblocking with, of protected DNA      224 342
Amphiphiles, synthetic      269 350—356
Ampicillin      311
ancat = anti-catenoid, definition      360
Androst-4-erie-3,17-dione, ( $\pm$ )-      280
Androst-5-en-17-one, 3-(acetyloxy)-, ( $3\beta$ )- (andro-stenolone acetate), partial synth.      118—119
Anellations      see “Carbocycles”
Angle of incidence in nucleophilic addns      315—316
Anisoles      see “Arenes alkoxy-”
Annealing of DNA primers      227
Annealing of sticky ends      225—226 243—244
Annulenes, bridged      38 123—124 333—334
Anthracene, 9-(chloromethyl)-, mutagen      341—342
Anthracene, Diels — Alder addn. to      93
Anti/syn-selectivity      see “cis/trans-selectivity” “erythro/threo-selectivity”
Antibiotics, synth.      310—329 (see also “Griseofulvins”)
Antithesis      171 193
Arabinose      D— and L— pr 263
Arborol      355—356
Arenes, alkoxy-, reduction      87 97 103—104
Arenes, electrophilic substitution at      207—208 305—306 309
Arenes, nucleophilic substitution at      42—43 305 310
Arenes, redn., with $\mathrm{H_{2}}$ /catalyst      87 112—113
Arenes, redn., with Li or Na      87 97 103—104
Arenes, synth. by dehydrogenation      139—140 338
Arnstein tripeptide      313—314
Aromadendrene      32
Aromadendrene, cyclopropa[a]naphthalene precursor      85
Artemisia alcohol      45
Aspartic acid, pr.      184
Aspartic acid, protection      229
Aspirin      301
Asymmetric induction      see “Enantioselective”
Asymmetric induction, chiral ketones      62 106—107
Asymmetric induction, chiral sulfoxides      8—9
Asymmetric induction, steroid synthesis      27 278—281
Asymmetric syntheses      see “Enantioselective ...”
Asymmetry of vesicle membranes      351
Atropisomers, 5,10,15,20-tetraarylporphyrins      253
Atropisomers, Kemp’s acid arylimides      347
Atropisomers, porphyrin oligomers      348—349
Atropisomers, “binap” chelands      102—103
Axial/equatorial stereoselectivity, 1-alkylation of cyclic ketones with 1-alkynes      63
Axial/equatorial stereoselectivity, 1-alkylation of cyclic ketones with Cu and Zn organyls      44—45
Axial/equatorial stereoselectivity, 1-alkylation of cyclic ketones with sulfur ylides      45
Axial/equatorial stereoselectivity, 2-alkylation of cyclic enamines      13 25—26 73
Axial/equatorial stereoselectivity, 2-alkylation of cyclic hydrazones      12
Axial/equatorial stereoselectivity, 3-alkylation of cyclic enones      20 72
Axial/equatorial stereoselectivity, dihydroxylation of cycloalkenes      127—129
Axial/equatorial stereoselectivity, epimerization of alcohols      288
Axial/equatorial stereoselectivity, reduction of ketones      105—107
Azepines, hexahydro- (azepanes)      149 304
Azides, acyl-      see “Carboxylic acids azides”
Azides, heterocycles from      153—154
Azides, reduction to amines      267
Azines, olefins from      35
Aziridines, alkene + amine, $\mathrm{Pb(OAc)_{4}}$       212—213
Aziridines, alkene + amine, cyclization of 2-halo amines      154
Aziridines, alkene + amine, thermal decomposition of azides      154
Azlactones      see “5(4H)-Oxazolones”
Azodicarboxylic acid      see “Diazenedicarboxylic acid”
Bacteria, genetic engineering with      241—246
Baeyer — Villiger rearrangement      80 136—137 165 210 275—276 282 283 319—320
Baldwin rules      315—316
Barbaralone = $tricyclo[3.3.1.0^{2,8}]nona-3,6-dien-9-one$       94

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